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Brookline Vacation Rentals

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The Longfellow Lookout - Boston, MA Vacation Rental

The Longfellow Lookout

Boston, MA
1 Bed 1 Bath Sleeps 4
115 115 115 115 115 170 170 125 125 125 125 125 190 190 130 130 130
South End Retreat - Boston, MA Vacation Rental

South End Retreat

Boston, MA
0 Bed 1 Bath Sleeps 3
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City Views at Carlyle - Boston, MA Vacation Rental

City Views at Carlyle

Boston, MA
1 Bed 1 Bath Sleeps 4
- - 99 99 99 - - - - - - - - - 115 115 -
Archstone Indigo - Boston, MA Vacation Rental

Archstone Indigo

Boston, MA
1 Bed 1 Bath Sleeps 4
115 115 115 99 - - - - - - - - - 160 140 140 135
Archstone Modernity - Boston, MA Vacation Rental

Archstone Modernity

Boston, MA
1 Bed 1 Bath Sleeps 4
- 99 99 99 - - - 99 99 - - - - 150 - - -
West End Hideaway - Boston, MA Vacation Rental

West End Hideaway

Boston, MA
1 Bed 1 Bath Sleeps 4
- - - - - - - - 99 - - - - - - - -
South End Getaway - Boston, MA Vacation Rental

South End Getaway

Boston, MA
0 Bed 1 Bath Sleeps 3
99 99 99 - - - - 99 99 - - - - - - - -
Bird's Eye View - Boston, MA Vacation Rental

Bird's Eye View

Boston, MA
1 Bed 1 Bath Sleeps 4
- - - 99 - - - - - - - - - - - 115 -
Carlyle Penthouse - Boston, MA Vacation Rental

Carlyle Penthouse

Boston, MA
1 Bed 1 Bath Sleeps 4
99 - - - 99 - - - - 99 - - - - - - 125
Seaport Signal Building - Boston, MA Vacation Rental

Seaport Signal Building

Boston, MA
1 Bed 1 Bath Sleeps 4
- 99 99 99 99 - - - - - - 125 160 - - - -
Saint George - Boston, MA Vacation Rental

Saint George

Boston, MA
1 Bed 1 Bath Sleeps 4
- 99 99 99 - - - - 99 - - - - - 120 125 125
Back Bay Elegance - Boston, MA Vacation Rental

Back Bay Elegance

Boston, MA
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - - - - - 295
Fenway  Family Fun! - Boston, MA Vacation Rental

Fenway Family Fun!

Boston, MA
3 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - - -

About Brookline

A true Massachusetts gem, our Brookline vacation rentals represent a perfect fusion of classic New England charm with the high-end, refined society influence of modern Boston. As the childhood home to John F. Kennedy and his siblings, it's not hard to image a young JFK strolling under the changing foliage along the winding streets of this quaint town. Although stunning in every season, Brookline looks like a living holiday card under sparkling snow in winter months and boasts its true colors in the oranges and crimsons of autumn. Bustling Boston is only a 24 minute T ride on the Green Line from the local station, but there are plenty of fine dining options, historic sites, and shopping destinations to keep both country and city mice occupied in this charming destination!

Things to Do in Brookline

Dripping in vintage allure, The Coolidge Corner Theater is the Boston area's only non-profit independent movie theater, presenting current indie flicks and art house films alongside high-definition broadcasts from Europe's Grand Opera and London's National Theater. A hub of culture and retro style, it's considered one of Brookline's greatest treasures and a visit is certainly worth the ticket price of your movie of choice!

For an unexpected entertainment experience, take the kids to a performance at the Puppet Showplace Theater. Boasting a variety of shows and puppet-centric events (ranging from opportunities to meet the actors to adult summer classes) each show features high quality props, sets, and puppets for a uniquely mesmerizing theater experience.   

Fine dining in Brookline isn't hard to come by and refined palettes will rejoice at the selection of choices this destination has to offer! Savor and share a variety of tapas at Barcelona or enjoy a feel-good foodie experience with local farm to table cuisine at Lineage. Try contemporary twists on classic American pub food at The Abbey or opt for a "skillfully crafted sandwich" from Cutty's.

Brookline's Historical Experiences

Former President John F. Kennedy and his siblings called this Boston suburb home during their younger years and you'll find references to this famous family throughout Brookline. A must-see for history buffs, the John F. Kennedy National Historic Site modestly sits on a quiet, tree-lined street. Here, visitors can indulge their nostalgia for and fascination with the family that lived there nearly 100 years ago!

The Frederick Law Olmsted National Historic Site is a museum in the former home of American landscape architect Frederick Law Olmsted. Not only is it rich with historical anecdotes and artifacts from the life and work of a man who designed Boston's Emerald Necklace and NYC's Central park, the home itself represents the classic stateliness of old school New England and perches on immaculately kept grounds. 

Once you've learned about the man behind the design of the natural sanctuary, visit the Larz Anderson Park, a particularly idyllic part of the famed Emerald Necklace. Amble on a leisurely self-guided tour of the grounds or pack a picnic for a peaceful lunch by the placid pond!

Day Trips From Brookline

Our Brookline vacation rentals are the ideal place to stay if you're looking for easy access to Boston. Hop on the Green Line at the Brookline Village Station and you're only 24 minutes away from Bean Town, a sprawling metropolis where America's colonial history melds with modern shopping and dining in an atmosphere abuzz with city pride!

Continue your American history lesson with witchcraft, haunted lore, and more spooky happenings from our nation's past in Salem, approximately 22 miles to the north. Beach-goers will take delight in the sand and sun in Newbury and Plum Island, both about 40 miles north. 

Brookline is an artful blend of old and new, with contemporary city touches fusing amiably with the warmth and stateliness of classic New England. Whether you're visiting for the history, the proximity to Boston, or to fulfill a personal fantasy of being a member of the glamorous and intriguing Kennedy family, you're sure to fall for the quaint yet refined charm awaiting in the once-cobblestone streets of this beautiful town when you stay in a Brookline vacation rental! 

Photo credit: Nicholas Johnson via Flickr

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